Questions tagged [inductive-effect]

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What is the order of inductive effect among amines and N-alkyl amines?

What will be the order of inductive effect among -NH2 -NR2 and -NHR? (I read somewhere that it would be -NR2> -NH2. Is this correct and if so why? Where will -NHR fit in?)
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What is the order of inductive effect among the following groups?

What will be the order of inductive effect among carboxylic acid and acid derivatives? (My guess is that it is acid anhydride> carboxylic acid> ester> acid chloride> amide based on ...
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Does the electron displacement effect act only on sigma electrons?

Our teacher told us that the inductive effect or the electron displacement effect can only affect the sigma electrons. I did not understand why this should be. I reasoned it can not affect the pi ...
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41 views

Carbanion Stability order [duplicate]

Why is a 3° Carbanion unstable than 1° Carbanion? Carbon atom with negative charge will become little electropositive relative to a neutral carbon. So if a Carbanion is attached to three neutral ...
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Inductive effect of Alkyl group in Carbanions

in Carbanions, why are alkyl groups considered to have +I effect? Like O- Negative charge on carbon should make it relatively electropositive and so akyl groups should have -I effect essentially. C of ...
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1answer
58 views

The most acidic hydrogen among ethane, ethene, ethyne and allene

Among $$\ce{CH3-CH3}\qquad\ce{CH2=CH2}\qquad\ce{HC≡CH}\qquad\ce{CH2=C=CH2}$$ I need to find out the one having highest acidic hydrogen. As per my observations, there are two equivalent resonating ...
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1answer
102 views

Ortho-para directing and meta directing groups: Activating or deactivating the aromatic ring?

Determine the reactivity of the above compounds (activating or deactivating; ortho-para or meta directing). Explain your answers. You may use resonance structures in your explanation. Which molecule ...
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2answers
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Does Cl- Have more -I effect or +M effect ( Resonance effect)?

In this question my answer was (A) because i though $\ce{NH2}$ group would give more electrons than $\ce{Cl-}$ . But the correct answer is (D) and my teacher's reason is that chlorine has more ...
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Basic strength of piperidine and cyclohexyl amine [duplicate]

How can we justify that cyclohexyl amine is less basic than piperidine. According to me the inductive effect should be more in cyclohexyl amine as cyclohexane is a strong +inductive group but also ...
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1answer
34 views

Inductive effect of -NHMe

Why does $\ce{-NHMe}$ show -I effect. I think it should be opposite. I know that $\ce{-Me}$ groups are electron donating in nature. So the nitrogen atom will have a small $\delta^-$ charge. So then ...
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Methyl group and acidic nature [duplicate]

After reading various answers here on StackExchange (like Why is the methyl group electron-donating via the inductive effect? and Strongest negative inductive effect group between trimethylammonium, ...
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1answer
50 views

Why is formic acid stronger than acetic acid [duplicate]

Even when acetate ion is stabilized due to resonance why is it a weaker acid than formic acid. It is true that acetic acid has +I effect due to methyl group present on it but resonance is a stronger ...
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Problem in defining the Inductive effect

Inductive effect is introduced in many textbooks by giving an example of an alkyl halide $R-X$. The bond C1-X is polar due to electronegativity difference, therefore X gains partial negative charge ∆(-...
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1answer
57 views

Stability of carbocation directly attached to a halogen atom [duplicate]

I have two compounds.. How is the first one more stable? As I have been taught that -I effect of Chlorine dominates its +R effect but to explain this case, My teacher is saying that because of the ...
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1answer
48 views

Para effects on substituents in aromatic compounds

I wanted to know how to compare the following compounds on basis of acidic strength. I have to find the acidic strength of following compounds with $\mathrm{X}=\ce{CH3, \ OCH3,}$ and $\ce{NO2}$. For ...
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Comparison of basicity of Aniline, p-Anisidine, and o-Anisidine [duplicate]

I have a question where I am required to compare the basicity of Aniline, o-Anisidine, and p-Anisidine. Now here's what I do know:- In ortho substituted aniline, an ortho effect acts which reduces ...
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Comparison between groups with -I effects

So I have a few questions in my book that require me to compare between two different groups on the basis of their -I effects. I have a few questions on this that have been bugging me for quite a ...
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1answer
233 views

Effect of phenyl and vinyl substituents on Acidity of carboxylic

Recently I came across this statement in my textbook: Direct attachment of groups such as phenyl or vinyl to the carboxylic acid, increases the acidity of corresponding carboxylic acid contrary ...
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3answers
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Odd looking carbocation stability order [duplicate]

I am studying introductory organic chemistry, suddenly this one started looking odd, The carbocation stability for three compounds as given by my book is shown below, Let me call those as ...
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1answer
79 views

Change in inductive effect of a susbstituent when -R group replaces -H atom

There are several examples where the negative inductive effect of a substituent gets increased when a hydrogen atom on that substituent is replaced by an alkyl group. Some particular examples: $$\ce{...
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29 views

Trimethylsilyl vs tert-butyl as activating substituent of benzene

Would trimethylsilane as a benzene substituent have an activating effect relative to tert-butyl for electrophilic substitution reactions?
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1answer
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Why O and N promote SN1 but C=O inhibit SN1 although both are electron-withdrawing?

Source: Jonathan Clayden, Nick Greeves, Stuart Warren, Organic Chemistry 2th Edition, 339. The general idea I got so far, is that, carbocation will be more stable if the + charge at central C is ...
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How does the relative acidity of 2,3-dinitrophenol compare to that of 2,4-dinitrophenol?

I am assuming that the -I inductive effect in 2,3-dinitrophenol is stronger than in 2,4-dinitrophenol since it operates through less bonds, therefore on inductive grounds it should have a lower $\...
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1answer
135 views

What is the stability order of the carbocation and carboanion?

So I came up with examples as below: 1 2 Now I am confused about the +I and -I effect in these structures since to my knowledge it can only be applied when there is a substituent (I might be wrong)...
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139 views

Which substitutent should be placed on axial position in SCl2(OCH3)2?

According to Bent's rule, in $\mathrm{sp^3d}$ more electronegative element is placed on the axial position, so between $\ce{Cl}$ and $\ce{OCH3}$ in $\ce{SCl2(OCH3)2}$ which should be placed on axial ...
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Does an electronegative atom which carries a negative formal charge withdraw electrons by induction?

Electronegative atoms withdraw electrons by their inductuve effect. Does this fact remain true even when they are heavily loaded with electrons through negative formal charge? Are these two ideas ...
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1answer
93 views

Inductive effect of alkyl ammonium groups

Why $\ce{-NR3+}$ has more -I effect than $\ce{-NH3+}?$ And what about order of $\ce{-NHR2+}$ and $\ce{-NH2R+}?$ My attempts I got idea about electronegativity of carbon atom in $\ce{R}$ is more than ...
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386 views

Which of the following groups show +M and -I effect?

Which of the following group show +M and -I effect? (A) $\ce{-\underset{\underset{\huge O}{||}}{C}-F}$ (B) $\ce{-\underset{\underset{\huge O}{||}}{C}-OR}$ (C) $\ce{-O^-}$ (D) $\ce{-OH}$ Answer is ...
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2answers
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When 2-pentene reacts with HBr, what will be the major product?

If we consider the first step (formation of carbocation by the attack of the proton). A couple of textbooks I referred say that when the substituents on the $\ce{C=C}$ are different, the direction of ...
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1answer
139 views

Confusions about inductive effect and acid strength

If one of the hydrogens in the alkyl side chain of ethanoic acid is replaced with an atom of Chlorine, the acid has a larger Ka value. My book says this is since the Cl "borrows" electron density from ...
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1answer
207 views

Which of the two structures is more stable?

Which of the two structures is more stable? As far as I know, alkenes with a greater number of hyperconjugating structures are more stable. Hyperconjugation has a greater stabilizing effect than ...
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1answer
168 views

Does hyperconjugation into sigma-star explain methylamine's increased basicity relative to ammonia?

The inductive effect with the polarisation of the C-N bond obviously plays a role in stabilising the positive charge of the conjugate acid. But given the similar electronegativities for C and H, CH3 ...
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1answer
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Which Carbocation is most stable among the three? [closed]

According to me the answer should be (C) as that Carbocation will be stablized by resonance with Chlorine. I have read that resonance is the biggest deciding factor about the stability of a ...
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749 views

Why is C2H5 a stronger +I group than CH3?

While reading about the basic character of amines, I came across a note which said that $\ce{CH3-CH2-NH2}$ was more stable than $\ce{CH3-NH2}$ as $\ce{C2H5}$ was a stronger +I group than $\ce{CH3}$. ...
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1answer
538 views

Stability order of methy benzyl cations?

I know that meta position shown no resonance effect and hyperconjugation effect . So According to the order given I guess Hyperconjugating effect is taken into account as -CH3 has no Resonance effects....
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1answer
388 views

Give the order of nucleophilic addition reaction in the following -

I am confused that whether we should take only inductive or hyperconjugation effect also into consideration while finding the order. As the answer in the book is only according to inductive effect . ...
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Mechanism of substitution for disubstituted benzene

Here, I count the individual effects of the two oppositely directing groups. I assume that the deactivation of $\ce{NO_2}$ group at ortho and meta positions is higher. While bromination, I get the ...
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1answer
972 views

Comparing relative negative inductive effect of substituents (dialkyl amine, amine, alkoxide, fluoride)

Which of the following is correct with respect to the negative inductive effect of the substituents? 1. $\ce{-NR2 < -OR < -F}$ 2. $\ce{-NH2 < -OR < -F}$ 3. $\ce{-NR2 > -OR > -F}...
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Inductive effect of hydrogen isotopes

Why does the electron-donating inductive effect (+I) of the isotopes of hydrogen decrease in the order $\ce{T} > \ce{D} > \ce{H}$? (where T is Tritium and D is Deuterium) Google has nothing to ...